Great South Bay Bridge, aka the Captree Bridge, a twin-span bridge on the southwest side of Suffolk County, New York, on Long Island over the Great South Bay at Sunset

Holiday Homes in Shirley

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Check prices for these dates

In two weeks
26 June - 28 June
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Shirley holiday homes

Dining

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is AU$1,255
includes taxes & fees
7 July - 8 July
3 Story Beach Waterview, 3 KING bed, golf putting green!
Fridge, microwave, oven, stovetop

Tranquil Stay

Tranquil Stay
Shirley
8.0 out of 10, Very good, (10 reviews)
"Great stay! "
United States
Emily S.
The price is AU$860
includes taxes & fees
16 June - 17 June
Tranquil Stay
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is AU$957
includes taxes & fees
28 June - 29 June
Modern Vacation home. Close to The Hamptons
Terrace/patio

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AU$345
includes taxes & fees
15 June - 16 June
Spacious 3BR Family Home Near Everything
Shower, hair dryer, towels, soap

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (44 reviews)
"This place was the perfect location for us. Almost exact center between Jones beach and Port Jefferson. Clean and identical to what is shown."
United States
Marcus
The price is AU$251
includes taxes & fees
17 June - 18 June
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Smart TV, table football, books, stereo

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is AU$769
includes taxes & fees
15 June - 16 June
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Fridge, microwave, coffee/tea maker, electric kettle

Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is AU$487
includes taxes & fees
27 June - 28 June
Sundown Escape Near SouthShore University Hospital
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
Westhampton Beach
10.0 out of 10, Exceptional, (211 reviews)
"Great host, everything that we needed for our trip was available, ample room for the 9 of us."
United States
matthew p.
The price is AU$2,929
includes taxes & fees
10 July - 11 July
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
Smart TV

Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
10.0 out of 10, Exceptional, (4 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is AU$747
includes taxes & fees
15 June - 16 June
Peaceful private 2-bedroom house in Bayport. Amazing location!
Shower, hair dryer, soap, toilet paper

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$553
includes taxes & fees
21 June - 22 June
The Royal Suite - Ronkonkoma
TV

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
Rocky Point
7.4 out of 10, Good, (3 reviews)
"The house had everything we needed. I was laid out very well. It was comfortable. The outdoor space was nice."
United States
Carol
The price is AU$880
includes taxes & fees
15 June - 16 June
Charming Rocky Point Home ~ 1 Mi to Beach!
Exterior detail

Prime location, walk to all, cozy cottage Westhampton Beach

Prime location, walk to all, cozy cottage Westhampton Beach
Westhampton Beach
The price is AU$949
includes taxes & fees
28 June - 29 June
Prime location, walk to all, cozy cottage Westhampton Beach
Property grounds

Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
10.0 out of 10, Exceptional, (1 review)
"The host was very helpful and amazing. He also assisted us with transportation due to a mishap with our car rental. However if you want a peaceful and relaxing trip in Long Island please book this place. Reggie is an amazing guy .Thank you for hosting us"
United States
Lakisha M.
The price is AU$554
includes taxes & fees
25 June - 26 June
Bright & Comfortable Home in the Heart of It All
Outdoor dining

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
The price is AU$874
includes taxes & fees
29 June - 30 June
Hampton Bays Townhouse - Pool, Beach Access
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is AU$1,696
includes taxes & fees
16 June - 17 June
Black Swan Beachfront Home with Jacuzzi year round
Property grounds

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (29 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is AU$1,949
includes taxes & fees
15 June - 16 June
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Smart TV

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Fire Island
9.6 out of 10, Exceptional, (4 reviews)
"Perfect Fire Island getaway. Great location and beautiful beach home. Would recommend and love to come back!"
United States
Jessica W.
The price is AU$1,805
includes taxes & fees
15 June - 16 June
Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Interior

Breakwater Estate… perfect for Large Group Getaways!

Breakwater Estate… perfect for Large Group Getaways!
Mattituck
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is AU$2,488
includes taxes & fees
25 June - 26 June
Breakwater Estate… perfect for Large Group Getaways!
Shower, hair dryer, towels, shampoo

Villa Luz Home for US Open visitors w private pool

Villa Luz Home for US Open visitors w private pool
Hampon Bays
9.6 out of 10, Exceptional, (24 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is AU$2,412
includes taxes & fees
22 June - 23 June
Villa Luz Home for US Open visitors w private pool
Interior

Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
8.0 out of 10, Very good, (2 reviews)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is AU$1,333
includes taxes & fees
15 June - 16 June
Cozy beach hose minutes from Hamptons
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shirley Hotel Reviews

Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

8/10 Good
"The room was ready, clean and comfortable. Rather large. Air conditioning in room did not seem to work. Got s little warm overnight. Elevators had outages which led to some small waits. Casino was fun. All employees (check in, cleaning staff, casino staff and bistro) were friendly and helpful."
Cheryl 1-night trip
Posted less than an hour ago
Jake's 58 Casino Hotel - Adult Only

Find out more about Shirley

Shirley Holiday Homes information

Number of reviews
404
Accommodation
720 Holiday Homes
Lowest Price
AU$251
Highest Price
AU$2,929